4-nitro-2-(1H-phenanthro[9,10-d]imidazol-2-yl)phenol | 332073-14-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-nitro-2-(1H-phenanthro[9,10-d]imidazol-2-yl)phenol
• 英文别名: 6-(1,3-Dihydrophenanthro[9,10-d]imidazol-2-ylidene)-4-nitro-cyclohexa-2,4-dien-1-one
• CAS: 332073-14-0
• 化学式: C₂₁H₁₃N₃O₃
• 分子量: 355.353
• InChiKey: YKGJROCVAKPIDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-nitro-2-(1H-phenanthro[9,10-d]imidazol-2-yl)phenol 在 镍 、 肼 作用下， 以 乙醇 为溶剂， 以87%的产率得到4-amino-2-(1H-phenanthro[9,10-d]imidazol-2-yl)phenol
  参考文献：
  名称：

  具有大斯托克斯位移的Hg 2+的ESIPT特征“开启”荧光传感器和S 2–的顺序“关闭”检测以及在活细胞中的应用

  摘要：

  制备了具有大斯托克斯位移的Hg 2+激发态分子内质子转移（ESIPT）特征“开启”荧光传感器，然后它具有通过“关闭”荧光信号在水性介质中顺序检测S 2–的能力。。因此，合成了基于带有两个酚片段的菲[ 9,10 - d ]咪唑部分的简单荧光探针ol -PIP。ol- PIP探针由于聚集作用而随着水分数的增加逐渐显示出荧光增强。依次是ol -PIP的中等荧光发射通过连续添加约180 nm斯托克斯位移的Hg 2+连续地和选择性地照亮水性介质中的碘。此外，在存在S 2–的情况下，可以将持续的“开启”荧光强度淬灭至ol -PIP的原始状态。交替添加Hg 2+和S 2–可以使这种开关感应过程持续五次。Hg 2+和S 2–的检出限分别为6.45×10 –7和3.46×10 –7M。此外，ol -PIP已成功应用于Hg 2+真实水样中的检测；同时，具有低细胞毒性的ol -PIP也已成功用作生物成像试剂，用于检测活细胞中的Hg

  DOI：

  10.1016/j.jphotochem.2019.112165
• 作为产物：
  描述：

  3,5-二硝基-2-羟基苯甲醛 、 菲醌 在 ammonium acetate 、 溶剂黄146 作用下， 反应 1.5h， 以88%的产率得到4-nitro-2-(1H-phenanthro[9,10-d]imidazol-2-yl)phenol
  参考文献：
  名称：

  Ligand characteristics and in situ generation of Pd active species towards CC coupling using series of 2-(1H-imidazol-2-yl)phenols

  摘要：

  Series of systematically varied 2-(1H-imidazol-2-yl)phenol ligand frameworks, which were synthesized and properly characterized, have been used to investigate favourable ligand characteristics towards in situ formation of active palladium species in Suzuki-Miyaura coupling. Structures of 2-(4,5-diethy1-1Himidazol-2-y1)-4-nitrophenol (p-N similar to de) and 4-(tert-butyl)-2-(4,5-dipheny1-1H-imidazol-2-yl)phenol (p-tBu similar to dp) as well as the palladium complex of 2-(4,5-diethyl-1H-imidazol-2-y1)phenol (Pd.de(2)) were confirmed. Structural analyses show that para-nitro-substituted phenol moieties bear poor oxo-donor atom while the reverse was observed for para-dlu-substituted analogues. Ligand donor strengths were also determined by pK(a) analysis.Under the same reaction conditions for palladium catalyzed Suzuki-Miyaura coupling in the presence of 'ligand + palladium( II) acetate' catalyst system, results show that electronic properties of the ligands are more important than the variation in steric properties. In particular, ligands with strong bidentate chelate coordination potentials acted as poisons while those with monodentate coordination potential proved to be very beneficial towards in situ generation of superior active species. Furthermore, correlation between donor strength pKa data and the trends in catalytic efficiencies as a consequence of ligand presence was studied. Therefore, it was concluded that ligands with strong chelation tendencies adversely impacted in situ palladium catalyst generation efficiency and that there appears to be moderate steric requirement from ligands for optimal catalyst efficiency. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2014.02.032

文献信息

• Self-assembled superstructures derived from suitably substituted phenanthro[9,10-d] imidazole-based Zn(ii)/Cd(ii) complexes for selective detection of acetone
  作者：Mallayasamy Siva、Sheethal Sasi、Priya Rana、Raj Kumar Bera、Yuvaraj Sivalingam、Priyadip Das

  DOI：10.1039/d4nj00450g

  日期：——

  measurements using the SKP on the surfaces of films coated with superstructures derived from these metal complexes were carried out both in the dark and under UV (Ultra-Violet) illumination in the presence of different vapours of VOCs. As per the results, under UV illumination, the thin film fabricated with superstructures derived from Cd complexes ((L1)2M, (L2)2M and (L3)2M; M = Cd(II)) exhibit higher sensitivity

  智能材料的设计和开发在开发先进的挥发性有机化合物（VOC）传感平台方面引起了越来越多的关注。 π-共轭小有机结构单元可以自组装成有序的超结构，具有高比表面积、独特的光电性能、良好的化学/热稳定性和主客体相互作用能力等多重优势，使其成为具有吸引力的候选材料。 VOC 传感。然而，由于自组装过程中单体之间的非特异性相互作用，用具有可观电性能的 π 共轭结构单元制造稳定且有序的自组装结构及其在 VOC 选择性检测中的成功应用仍然是一个挑战以及在传感过程中分别与其他现有 VOC 的反应。在此，我们设计并合成了三种菲[9,10- d ]咪唑基配体；L1、L2和L3在 2 位具有三种不同的羟基苯类似物取代及其相应的 Zn( II ) 和 Cd( II ) 配合物，然后制造成具有离散形态的有序超结构，用于选择性检测丙酮蒸气使用扫描开尔文探针 (SKP) 测量接触电位差。一些实验分析表明，有效的非共价相互